WOOF Week 2026!
Experience the excitement of WOOF Week 2026 in Key West, featuring sizzling daytime and nighttime parties. The highlight of the event is electrifying performances by…
Free
54 events found.
Events for April 26, 2026
Ongoing
DJ Marty at Red Garter Saloon Stage
Experience the electrifying energy of DJ Marty at the Red Garter Saloon Stage. Known for his seamless mixing skills and dynamic performances, DJ Marty captivates…
Free
DJ Chaka at Rick’s Bar Upstairs Stage
DJ Chaka, the dynamic Key West entrepreneur and cancer survivor, electrifies Rick's Bar Upstairs Stage with his infectious energy and passion for life. Known as…
Free
Alex Anthony Band at Hog’s Breath Saloon
Experience the captivating performance of the Alex Anthony Band at Hog's Breath Saloon, where they redefine the modern cover band with seamless talent and an…
Free
The Tiki Bombs at Tiki House Key West
The Tiki Bombs, a dynamic band celebrated for their energetic performances, bring a tropical flair to Tiki House Key West. Blending traditional island melodies with…
Free
Durtbags at Durty Harry’s Stage
Experience the electrifying atmosphere of Key West with The Durtbags, the premier party rock band, at Durty Harry's Stage. Performing live from Thursday to Sunday,…
Free
Karaoke at Bobby’s Monkey Bar
Experience an unforgettable night of karaoke at Bobby's Monkey Bar, where the star of the show is the charismatic karaoke host. With their vibrant energy…
The Audio Files at Sloppy Joe’s Bar
Experience an unforgettable evening with The Audio Files at Sloppy Joe's Bar. Known for crafting rich, immersive auditory journeys, The Audio Files blend storytelling, meditative…
Free
Jack and Jim Show at Irish Kevin’s Bar
Experience the electrifying Jack and Jim Show at Irish Kevin's Bar in Key West. Renowned for dynamic performances, Jack and Jim captivate audiences with their…
Free
Karaoke w/ Jason at Rick’s Bar Downstairs Stage
Experience an unforgettable night with DJ Jason at Rick's Bar Downstairs Stage. Known for his electrifying beats and seamless mixes, Jason transforms karaoke into a…
Free
Yoga on the Beach – Ft Zachary Taylor
Join Yoga on the Beach at Fort Zachary Taylor State Park. This unique event combines the serene beauty of a historic beachside setting with invigorating…
$20
Chris at Two Friends Patio Restaurant
Experience the vibrant performance of Chris at Two Friends Patio Restaurant, a beloved Key West venue. Chris brings lively entertainment to the restaurant's charming open-air…
Free
Izzy Zaidman at Sloppy Joe’s Bar
Experience the captivating performance of Izzy Zaidman at Sloppy Joe's Bar, where his dynamic guitar skills and soulful compositions fill the historic Key West venue…
Free
Key West Artisan Market at Higgs Beach
The Key West Artisan Market at Higgs Beach offers an enchanting experience where visitors can explore crafts and local art. The highlight is the talented…
Marjory Lee at Rams Head Southernmost
Marjory Lee, a captivating musician from Key West, FL, enchants audiences with her soulful voice and expert guitar skills at Rams Head Southernmost. Crowned Fantasy…
Free
Bradd Shadduck at Irish Kevin’s Bar
Bradd Shadduck brings his electrifying musical talent to Irish Kevin's Bar, captivating audiences with his energetic performances. Nestled in the vibrant Duval Street of Old…
Free
Rick Fusco at Two Friends Patio Restaurant
Rick Fusco is an engaging musician performing live at Two Friends Patio Restaurant, a vibrant Key West venue known for its lively atmosphere. With his…
Free
Aaron Blumer at Hog’s Breath Saloon
Aaron Blumer, a dynamic musician often compared to a carefree tumbleweed, brings his adventurous spirit to the stage at Hog's Breath Saloon. Renowned for his…
Free
Sid The Bayou Kid at Sloppy Joe’s Bar
Sid The Bayou Kid enchants audiences at Sloppy Joe's Bar with his magnetic presence and soulful performances. This dynamic blues musician from Louisiana weaves storytelling…
Free
Mylo O’Maolain at Schooner Wharf Bar
Mylo O'Maolain lights up Schooner Wharf Bar with his vibrant performances, blending Irish traditions with contemporary flair. As an Irish-born entertainer and musician thriving in…
Free
Cayman & Company at Green Parrot Bar
Cayman & Company performs at the iconic Green Parrot Bar in Key West, bringing dynamic energy and vibrant live music to this historic venue. Known…
Free
Farm Open House
Join the Farm Open House at the Monroe County Sheriff's Office Animal Farm in Key West, featuring live entertainment that will captivate visitors of all…
Farm Open House
Join the Farm Open House at the Monroe County Sheriff's Office Animal Farm in Key West, a nonprofit sanctuary. Enjoy live entertainment alongside exotic birds…
Free
Jeff Harris at Irish Kevin’s Bar
Experience the dynamic talent of Jeff Harris at Irish Kevin's Bar, where his captivating blend of music and comedy takes center stage. Known for his…
Free
Aaron Hudgins at Tiki House Key West
Experience the enchanting performance of musician Aaron Hudgins at Tiki House Key West. Known for his captivating live music, Hudgins brings a dynamic energy to…
Free
Cayman & Company at Green Parrot Bar
Experience the vibrant sounds of Cayman & Company at the iconic Green Parrot Bar in Key West. Known for their innovative and dynamic performances, Cayman…
Free
Tea Dance at La Te Da
Experience the exuberance of Tea Dance at La Te Da, one of Key West's most dynamic venues. Renowned for dazzling drag shows featuring the charismatic…
Free
Josh Kiser at Mac’s Place
Josh Kiser, a talented singer-songwriter from Cleveland, Tennessee, captivates audiences with his soulful blend of traditional '90s sounds and emotive storytelling. Based in Key West,…
Free
801 Karaoke – Hosted by Jeff
Join Jeff at 801 Bourbon Bar for an unforgettable karaoke experience in the heart of Old Town Key West. As an engaging and charismatic host,…
Free
Ross Brown Duo at Hog’s Breath Saloon
The Ross Brown Duo brings a captivating musical experience to Hog's Breath Saloon in Key West. Ross Brown, a talented musician and self-proclaimed Spiritual Gangster,…
Free
World Famous 801 Girls- 5pm Show
Experience the dazzling World Famous 801 Girls at their 5pm show, where these talented drag queens bring glamour and energy to the stage. Held at…
QMitch Drag Queen Bingo at 22&Co
Join the vibrant atmosphere of 22&Co in Old Town Key West for QMitch Drag Queen Bingo. Hosted by the charismatic QMitch, this event promises an…
Free
Sunday Jazz at the Gardens
Enjoy a delightful evening at Sunday Jazz at the Gardens, featuring acclaimed jazz artists who bring soulful melodies to life in a serene tropical setting.…
Free
Rick Fusco at Rams Head Southernmost
Rick Fusco captivates audiences at Rams Head Southernmost with his musical talent. As a seasoned musician, Fusco delivers engaging performances that complement the vibrant, island…
Free
Conch Country Dance Party
Join the Conch Country Dance Party and experience the captivating live country music of Where’s Dave. Set in the historic Key West Woman's Club courtyard,…
Free
Sunset Celebration at Mallory Square
At Mallory Square's Sunset Celebration, experience Key West's lively atmosphere featuring a host of talented entertainers, including jugglers and the celebrated cat man. Against a…
Free
Caribe of Key West at El Meson de Pepes on Mallory Square
Experience the lively beats of Caribe of Key West at El Meson de Pepes on Mallory Square. This talented group energizes the atmosphere with their…
Shanty Hounds at Two Friends Patio Restaurant
Shanty Hounds is a dynamic acoustic duo from Key West, featuring Dani Hoy and Key West Chris Rehm. Their spirited performances at Two Friends Patio…
Free
Tim Palmieri & Friends Soundcheck Set at Green Parrot Bar
Experience an unforgettable evening as Tim Palmieri & Friends take the stage for a soundcheck set at the Green Parrot Bar. Renowned for his virtuosic…
Free
Pete & Larry Sloppy 2nds at Sloppy Joe’s Bar
Experience the eclectic creativity of Pete & Larry in their dynamic project, Sloppy 2nds, at Sloppy Joe's Bar in Key West. Blending humor with innovation,…
Free
Jerome & Wynn at The Alamo Key West
Experience the remarkable synergy of Jerome & Wynn at The Alamo Key West. Known for their creative collaboration and innovative approach, this talented duo captivates…
Free
Oren Polak at Irish Kevin’s Bar
At Irish Kevin's Bar, Oren Polak mesmerizes audiences with his versatile musicianship and charismatic stage presence. Known for his captivating performances, he delivers a unique…
Free
80s & 90s Trivia Night
Join us for a memorable 80s & 90s Trivia Night at The Retro Room in Old Town Key West. Relive the good times with our…
Free
42nd Annual Schooner Wharf Wreckers Cup Race 2026 Season Awards Party
Celebrate the 42nd Annual Schooner Wharf Wreckers Cup Race 2026 Season Awards Party at the lively Schooner Wharf Bar in Key West. Relish a BBQ…
Free
Jesse & Jillian at Schooner Wharf Bar
Jesse & Jillian, known as The Happy Dog, are an electrifying music duo performing at Schooner Wharf Bar in Key West. Renowned for their captivating…
Free
Graham Nash at Key West Theater
Experience the legendary Graham Nash at Key West Theater, where his captivating melodies and timeless classics will fill the intimate venue. As a pioneering figure…
$
Jack Wolf at Halo Rooftop Lounge Bar at The Saint
Experience the soulful sounds of Jack Wolf at the Halo Rooftop Lounge Bar. As a talented singer-songwriter based in Key West, Jack captivates audiences with…
Free
Ronnie Lovely at La Te Da
Experience the captivating allure of Ronnie Lovely at La Te Da in Key West. As a talented musician, Ronnie brings his unique style to the…
Free
Magic Of Frank Everhart at Schooner Wharf Bar
Experience the enchanting Magic of Frank Everhart at Schooner Wharf Bar, where the legendary magician captivates audiences with his innovative tricks and spellbinding storytelling. Frank's…
Free
Nick Walker at Tiki House Key West
Experience the captivating artistry of Nick Walker at Tiki House Key West. A renowned muralist from Bristol, UK, Walker brings his contemporary street art flair…
Free
Alex Anthony Band at Hog’s Breath Saloon
Experience the dynamic energy of the Alex Anthony Band at Hog's Breath Saloon in Key West. Renowned for revolutionizing the modern cover band scene, Alex…
Free
Karaoke at Bobby’s Monkey Bar
Experience lively karaoke nights at Bobby's Monkey Bar, set in the heart of Key West's Old Town. With an engaging entertainer leading the fun, guests…
Mylo O’Maolain at Irish Kevin’s Bar
Mylo O'Maolain captivates audiences at Irish Kevin's Bar with his energetic performances. Known for his engaging stage presence and musical talent, Mylo transforms the lively…
Free
The Audio Files at Sloppy Joe’s Bar
Experience The Audio Files at Sloppy Joe's Bar in Key West, where this innovative auditory ensemble captivates audiences with a rich tapestry of immersive soundscapes.…
Free